N-(7-(2-chlorophenyl)-5-ethynyl-2,6-naphthyridin-3-yl)cyclopropanecarboxamide → N-(7-(2-chlorophenyl)-5-ethyl-2,6-naphthyridin-3-yl)cyclopropanecarboxamide

HRID 1502376Notes

Reaction equation

HRID 1502376 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[N:14]=[CH:15]2)=[C:10]([C:24]#[CH:25])[N:9]=1>C(O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]3[CH2:22][CH2:23]3)=[O:20])[N:14]=[CH:15]2)=[C:10]([CH2:24][CH3:25])[N:9]=1

Participants

4

Reactant 1

HCID 86674952N-(7-(2-chlorophenyl)-5-ethynyl-2,6-naphthyridin-3-yl)cyclopropanecarboxamide

Product 1

HCID 68095400N-(7-(2-chlorophenyl)-5-ethyl-2,6-naphthyridin-3-yl)cyclopropanecarboxamideYield 56.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

N-(7-(2-chlorophenyl)-5-ethynyl-2,6-naphthyridin-3-yl)cyclopropanecarboxamide (40 mg, 0.1 mmol) was dissolved in ethanol (15 mL) and treated with platinum dioxide (3 mg, 0.01 mmol). The reaction flask was flushed with nitrogen and evacuated three times and then flushed with hydrogen gas, evacuated once, and then left under a balloon of hydrogen. The reaction mixture was stirred for 16 hours at room temperature and then filtered over a pad of Celite. The filtrate was evaporated in vacuo to afford a residue that was purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% ammonium hydroxide over 14 min) to afford the title compound as an off-white solid (20 mg, 50%). 1H NMR (400 MHz, DMSO) δ 11.16 (s, 1H), 9.31 (s, 1H), 8.78 (s, 1H), 8.08 (s, 1H), 7.77-7.69 (m, 1H), 7.61 (m, 1H), 7.54-7.42 (m, 2H), 3.24 (dd, J=15.2, 7.7 Hz, 2H), 2.15-2.07 (m, 1H), 1.38 (t, J=7.4 Hz, 3H), 0.95-0.80 (m, 4H). LCMS (Method E): RT=5.052 min, M+H+=352.1.

Workup

  1. customThe reaction flask was flushed with nitrogen
  2. customevacuated three times
  3. customflushed with hydrogen gas
  4. customevacuated once
  5. waitleft under a balloon of hydrogen
  6. filtrationfiltered over a pad of Celite
  7. customThe filtrate was evaporated in vacuo
  8. customto afford a residue that
  9. customwas purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% ammonium hydroxide over 14 min)

Sources & evidence

ORD record
ord-004db2c95b1744b2b4bfb0253cb364dd
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

Loading…